Supernatural Happenings in Stars Hollow
by Luck Dragon94
Summary: Alright, this is completely AU and written strictly for fun. Signs of the yellow eyed demon lead the Winchesters to Stars Hollow, where Sam is enrolled at Chilton and meets a certain young Gilmore girl...


Disclaimer: Sadly, I do not own Supernatural or Gilmore Girls or much of anything, really...

Okay… This is COMPLETELY AU and strictly just for fun. I just had a sudden desire to write a completely untrue guilty pleasure and let my imagination run wild. Besides, I hope that everyone who once watched Gilmore Girls will really like it. Sam is 17 and Dean is 21 – just so you know. Please enjoy it!

* * *

The Fiesta Motel, Indiana

John shuffled through the papers on the table for about the thousandth time. Same answer. All the signs led to Connecticut – lightning storms, dark smoke sightings, all things pointing to a demon. Well, _the _demon. Such_ a shame_, he thought, _we'll have to transfer Sammy again. This one might take a while. _He took a moment to breathe, then said, "Boys, I think we'll have to move again."

Dean jumped off the couch immediately, "Where to?"

"Connecticut… A little suburb of Hartford, actually. Some place called Stars Hollow. I, uh, tracked some signs, and I think we've got a job there. This one could actually be big, and it may take some time." He looked at Sam, "I'll talk to the principal tomorrow, Sam. We've gotta get a move on this one."

"But-" Sam sighed, knowing that arguing would be pointless… well, he had to try. "Dad, we just got here. I finally caught up on all this stuff, and I – well, I just hoped that I could stay at _one_ school for a while, especially since this one is actually good."

That didn't go over too well. "Sam, you know that this is our responsibility. If we have to make some sacrifices along the way, well then, we have to. Tomorrow will be your last day at that school, and that's final. We're moving." He was quiet for a minute, almost as if he was going to say something. "What are you two waiting for? Start packing."

Guess the moment passed.

* * *

Johnson High School, Indiana

"Well, class, your Renaissance papers are due on Tuesday, and I expect you to have read all of chapters 21 and 22 by tomorrow. Remember, I still haven't ruled out a pop quiz!"

Groan…

The bell rang. As the rest of the class rushed for the exit, Sam packed his backpack, pulled out the withdrawal for, and head straight for the teacher's desk. "Mr. Cummings? I, uh, need you to sign this."

Mr. Cummings sighed, taking off his glasses. "Yes, Sam, I know. The principal said your father had called. Nothing's wrong, is it?"

"No, Sir."

"Well, your family just got here, and it seems a bit odd that you would be moving again so quickly."

"My dad's job has him moving around a lot. It's no big deal or anything. But, uh, if it helps, I'll really miss your class. I actually had just caught up."

"I know. Well, Sam, I have a proposition for you. Your father said that you were going to Hartford, Connecticut. It just so happens that in Hartford there is one of the most prestigious prep schools in the nation, with quite the reputation of turning out Ivy League students. "

Sam looked down at his form. Where was this even going? A prep school? Like if his dad would ever even consider…

"I think you have a lot of potential, Sam. You have excellent grades, a dream of Stanford, great work ethic. I think Chilton could really use a student like you."

"Chilton, Sir?"

"Yes, dear boy, Chilton. I know a bit of your family's – er – financial situation. But, you don't have to worry about any of that. I am old friends with the headmaster of the school, and he thought it would be absolutely wonderful to have such a bright young man as a part of a scholarship program. All you have to do is keep your grades up, and you will receive the best education you could ask for. What do you think, hmm?"

Sam was stunned. Scholarship? Chilton? "Uh, Mr. Cummings? I don't even know if my dad will say yes. I don't even know if we'll be in Connecticut long. I don't even… I don't think he'll like the whole prep school thing. It's just… not us."

"My boy, I assure you that you will not regret it! Don't worry about a thing, not tuition, not uniforms. We will handle everything. To your father it will just seem like… a school! Nothing fancy, and I'm sure you were made for this." He beamed at Sam, "Now, let me sign these forms…"

* * *

The Impala, en route to Connecticut

"I just can't believe they think that I can't get you into a school myself."

"Dad, this isn't just any school… It's a private school, and a pretty expensive one at that. They just thought I'd do well there, fit in, you know?"

"Sam, it's just…" John paused, "it's just they didn't ask me. Hartford is 40 minutes from where we're staying, and this school just means that you won't have a lot of time to do your job. We're not going for fancy schools, remember? We have a job to do, and if it's as tough as they said, you'll have to make sacrifices."

"I know, Dad, but they went through all the trouble of getting me in and paying for stuff and _buying uniforms_. The least I could do is actually show up to this school."

John was quiet for a while. Finally he said, "Fine. But remember that once we're done there, we're going to move. Clear?"

"Yes, Sir. We're clear."

* * *

Chilton Academy, Connecticut

Ring!

Sam pushed his way through the crowded hallways feeling strangely out of place. Everyone stared as he passed – another new kid? Well, there wasn't much for it. He walked up to a group that looked pretty experienced, "Hey, uh, can you tell me where the headmaster's office is?"

On girl (who looked pretty uptight and stuck up) gave him a once over. "Yeah. It's down the hall and to the right. New, huh?"

"Uh, yeah," he held out his hand, "Sam Winchester."

"Paris Geller. I hope you can handle Chilton." She stalked off.

"Thanks?" _God, _he thought, _maybe this wasn't the best idea. What's up with her anyway?_

Sam walked down the hall and to the right and found himself at the secretary's desk. "Excuse me? Uh, I'm Sam Winchester, a new student?"

"I know who you are, and you're late. The headmaster is waiting for you in his office."

"Thanks…" He walked through very intimidating doors and came face-to-face with the headmaster himself.

"Ah, Mr. Winchester! My collegues at Johnson all had great things to say about you! However, I assure you that Chilton will be a challenge beyond anything you've experienced thus far in your educational career. As a student on scholarship here, I expect you to be the prime example of what this prestigious academy is all about – no slacking, no horseplay, and no nefarious activities. Now, I believe you should head to your class. The secretary will give you a schedule, your locker number and combination, and I'm sure will point you in the right direction of you classroom. Once again, Mr. Winchester, welcome to Chilton."

He led Sam out of the office and straight to the secretary's desk. Once he had been handed several pages of the honor code, school rules, locker information, and a class schedule, he finally headed to his first period.

He knocked on the door before entering. Mr. Medina signaled for him to enter, so he did. "Class, we have a new student joining us from Indiana – Sam Winchester, welcome to Chilton. Please, take a seat."

Sam, never having felt nervous on the first day of school before, found a seat next to a pleasant-looking girl with a bright yellow backpack. She looked up from her book and smiled at him. Sam felt the knot in his stomache loosen a bit as he managed a small smile in return. "Hi, I'm Sam."

"Yeah, I figured. I'm Rory – well, Loralei actually, after my mom, but everyone knows me as Rory." She said all this very quickly.

"Okay, Rory. It'g good to meet you," he managed another smile.

"Yeah, good to meet you too."


End file.
